Flavonoid compounds, and methods of use thereof

A compound of the general formula (I):

• wherein
• X represents an NH, S or O;
• Y1, Y2, Y3, Y4 are independently selected from C or N;
• R1, R2 and R4 are independently selected from the group comprising hydroxyl, haloalkyl, haloalkoxy, heterocyclic and substituted heterocyclic, —NH2, —NH(lower alkyl) and —N(lower alkyl)2;
• R3, R9 and R10 are independently selected from the group comprising H, halogen and lower alkyl;
• R5, R6, R7 and R8 are independently selected from the group comprising H, lower alkyl, halogen, hydroxyl, ester, haloalkyl, haloalkoxy, heterocyclic, substituted heterocyclic, —NH2, —NH(lower alkyl), and —N(lower alkyl)2;
• or
• a pharmaceutically acceptable salt, hydrate, solvate, prodrug and isomer thereof;
• with the proviso that at least one of R1, R2, R3, R4, R5, R6, R7 and R8 is selected from the group comprising haloalkyl, haloalkoxy, heterocyclic, substituted heterocyclic, —NH2, —NH(lower alkyl) and —N(lower alkyl)2;
• with the proviso that the compound is not selected from the group comprising:
• 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzothiopyran-4-one;
• 2-(2,3-dihydroxyphenyl)-5,8-dihydroxy-4H-1-benzothiopyran-4-one;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,7-dihiydroxy-4(1H)-quinolinone, hydrobromide;
• 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4(1H)-quinolinone, hydrobromide;
• 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,6,7-trihydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-5,7-dimethyl-4(1H)-quinolinone, hydrobromide;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-5,7-dimethyl-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-7-methoxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-6-methoxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3,6,7,8-tetrahydroxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-5-methoxy-4(1H)-quinolinone;
• 2-(3,4-dihydroxyphenyl)-3-hydroxy-6,7-dimethoxy-4(1H)-quinolinone;
• 2-(3-amino-4-hydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one;
• N-[2-(3-amino-4-hydroxyphenyl)-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl]-acetamide;
• N-[3-hydroxy-2-[4-hydroxy-3-[91-methylethyl)amino]phenyl]6-methyl-4-oxo-4H-1-benzopyran-8-yl]-acetamide;
• N-[2-hydroxy-5-(3-hydroxy-6-methyl-4-oxo-4H-1-benzopyran-2-yl)phenyl]-acetamide;
• 2-(3-amino-4-hydroxyphenyl)-3-hydroxy-6-methyl-4H-1-benzopyran-4-one;
• 8-amino-2-(3-amino-4-hydroxyphenyl)-3-hydroxy-6-methyl-4H-1-benzopyran-4-one;
• N-[2-Hydroxy-5-(3-hydroxy-6-methyl-4-oxo-4H-1-benzopyran-2-yl)phenyl]-acetamide;
• N-[2-(3,4-dihydroxyphenyl)-3-hydroxy-4-oxo-4H-1-benzopyran-6-yl]-acetamide;
• N-[2-(3-amino-4-hydroxyphenyl)-3-hydroxy-6-methyl-4-oxo-4H-1-benzopyran-8-yl]-acetamide;
• 6-acetamido-3-hydroxy-4′-methoxy-flavone;
• 3,3′-dihydroxy, 6,7-dimethyl,4′-(pyrrolidine-1-yl)-flavone;
• and
• 2-(3-amino-4-hydrophenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one.

A method of preventing and/or mitigating the damage caused by cell apoptosis and/or cell necrosis, the method comprising:

• administering a therapeutically effective amount of at least one compound in accordance with the following general formula:
• wherein
• X represents an NH, S or O;
• Y1, Y2, Y3, Y4 are independently selected from C or N;
• R1, R2 and R4 are independently selected from the group comprising hydroxyl, haloalkyl, haloalkoxy, heterocyclic, substituted heterocyclic, —NH2, —NH(lower alkyl) and —N(lower alkyl)2;
• R3, R9 and R10 are independently selected from the group comprising H, halogen and lower alkyl;
• R5, R6, R7 and R8 are independently selected from the group comprising H, lower alkyl, halogen, hydroxyl, ester, haloalkyl, haloalkoxy, lower alkoxy, heterocyclic, substituted heterocyclic, —NH2, —NH(lower alkyl), and —N(lower alkyl)2;
• or
• a pharmaceutically acceptable salt, hydrate, solvate, prodrug and isomer thereof;
• with the proviso that at least one of R1, R2, R4, R5, R6, R7 and R8 is selected from the group comprising haloalkyl, haloalkoxy, heterocyclic, substituted heterocyclic, —NH2, —NH(lower alkyl) and —N(lower alkyl)2.